#------------------------------------------------------------------------------
#$Date: 2017-05-06 01:10:09 +0300 (Sat, 06 May 2017) $
#$Revision: 196447 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/04/25/7042518.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7042518
loop_
_publ_author_name
'Megger, Dominik A.'
'Rosowski, Kristin'
'Radunsky, Christian'
'Kösters, Jutta'
'Sitek, Barbara'
'Müller, Jens'
_publ_section_title
;
 Structurally related hydrazone-based metal complexes with different
 antitumor activities variably induce apoptotic cell death.
;
_journal_issue                   14
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              4759
_journal_page_last               4767
_journal_paper_doi               10.1039/c6dt04613d
_journal_volume                  46
_journal_year                    2017
_chemical_formula_sum            'C24 H30 Cl4 Mn2 N8 O3'
_chemical_formula_weight         730.24
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2016-10-20 deposited with the CCDC.
2017-03-17 downloaded from the CCDC.
;
_cell_angle_alpha                97.0030(10)
_cell_angle_beta                 101.4300(10)
_cell_angle_gamma                109.0230(10)
_cell_formula_units_Z            1
_cell_length_a                   7.06430(10)
_cell_length_b                   9.7937(2)
_cell_length_c                   11.6995(2)
_cell_measurement_reflns_used    7866
_cell_measurement_temperature    153(2)
_cell_measurement_theta_max      30.09
_cell_measurement_theta_min      2.59
_cell_volume                     734.70(2)
_computing_cell_refinement       'SAINT V8.18C (Bruker AXS Inc.)'
_computing_data_collection       'APEX2 v2012.2-0'
_computing_data_reduction        'SAINT V8.18C (Bruker AXS Inc.)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      153(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'APEX-II CCD-detector'
_diffrn_measurement_method       'omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0163
_diffrn_reflns_av_unetI/netI     0.0172
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            12944
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.093
_diffrn_reflns_theta_min         1.813
_diffrn_source                   Microfocus
_exptl_absorpt_coefficient_mu    1.266
_exptl_absorpt_correction_T_max  0.7460
_exptl_absorpt_correction_T_min  0.6570
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2008/1 (Bruker AXS)'
_exptl_crystal_colour            pink
_exptl_crystal_density_diffrn    1.650
_exptl_crystal_description       wedge
_exptl_crystal_F_000             372
_exptl_crystal_size_max          0.418
_exptl_crystal_size_mid          0.354
_exptl_crystal_size_min          0.308
_refine_diff_density_max         0.440
_refine_diff_density_min         -0.357
_refine_diff_density_rms         0.053
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     234
_refine_ls_number_reflns         4284
_refine_ls_number_restraints     9
_refine_ls_restrained_S_all      1.045
_refine_ls_R_factor_all          0.0278
_refine_ls_R_factor_gt           0.0248
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0323P)²+0.3120P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0641
_refine_ls_wR_factor_ref         0.0661
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3915
_reflns_number_total             4284
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c6dt04613d2.cif
_cod_data_source_block           cr170412_0m
_cod_depositor_comments
'Adding full bibliography for 7042517--7042519.cif.'
_cod_database_code               7042518
_shelx_shelxl_version_number     2014/7
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min   0.620
_shelx_estimated_absorpt_t_max   0.696
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Mn1 Mn 0.26518(3) 0.21385(2) 0.24459(2) 0.01828(6) Uani 1 1 d . . . . .
Cl1A Cl 0.23033(12) -0.01350(11) 0.1124(2) 0.0300(4) Uani 0.563(5) 1 d . . P A
1
Cl1B Cl 0.22235(16) -0.02918(10) 0.1648(3) 0.0304(4) Uani 0.437(5) 1 d . . P A
2
Cl2 Cl 0.66247(5) 0.32818(3) 0.29948(3) 0.02278(7) Uani 1 1 d . . . . .
O1A O 0.9050(6) 0.1231(5) 0.1836(3) 0.0233(6) Uani 0.563(5) 1 d D . P A 1
H1A H 0.842(3) 0.175(2) 0.209(2) 0.029(10) Uiso 0.563(5) 1 d D . P A 1
H1B H 0.863(5) 0.097(4) 0.1092(5) 0.063(13) Uiso 0.563(5) 1 d D . P A 1
O1B O -0.0685(7) 0.1580(5) 0.2212(4) 0.0238(8) Uani 0.437(5) 1 d D . P A 2
H1C H -0.130(3) 0.216(2) 0.235(4) 0.064(19) Uiso 0.437(5) 1 d D . P A 2
H1D H -0.151(4) 0.083(2) 0.171(3) 0.03(2) Uiso 0.437(5) 1 d D . P A 2
N1P N 0.25875(16) 0.17382(12) 0.42874(10) 0.0216(2) Uani 1 1 d . . . . .
C2P C 0.25545(18) 0.28218(14) 0.50842(11) 0.0194(2) Uani 1 1 d . . . . .
C3P C 0.26010(19) 0.27260(15) 0.62726(12) 0.0237(2) Uani 1 1 d . . . . .
H3P H 0.2593 0.3522 0.6821 0.028 Uiso 1 1 calc R U . . .
C4P C 0.2659(2) 0.14428(16) 0.66260(13) 0.0284(3) Uani 1 1 d . . . . .
H4P H 0.2672 0.1339 0.7424 0.034 Uiso 1 1 calc R U . . .
C5P C 0.2696(2) 0.03050(16) 0.58074(14) 0.0297(3) Uani 1 1 d . . . . .
H5P H 0.2746 -0.0584 0.6035 0.036 Uiso 1 1 calc R U . . .
C6P C 0.2661(2) 0.04968(15) 0.46591(13) 0.0255(3) Uani 1 1 d . . . . .
H6P H 0.2689 -0.0281 0.4099 0.031 Uiso 1 1 calc R U . . .
N1R N 0.24552(17) 0.40868(12) 0.46983(9) 0.0202(2) Uani 1 1 d . . . . .
H1R H 0.2344 0.4814 0.5169 0.024 Uiso 1 1 calc R U . . .
N2R N 0.25397(16) 0.41415(11) 0.35548(9) 0.01836(19) Uani 1 1 d . . . . .
C2R C 0.23984(17) 0.52428(12) 0.30935(10) 0.0172(2) Uani 1 1 d . . . . .
C1M C 0.2100(2) 0.65433(13) 0.37286(11) 0.0218(2) Uani 1 1 d . . . . .
H2M H 0.3447 0.7265 0.4188 0.033 Uiso 1 1 calc R U . . .
H1M H 0.1219 0.6224 0.4268 0.033 Uiso 1 1 calc R U . . .
H3M H 0.1437 0.6995 0.3147 0.033 Uiso 1 1 calc R U . . .
N1Q N 0.24365(15) 0.37822(11) 0.12872(9) 0.01848(19) Uani 1 1 d . . . . .
C2Q C 0.24937(17) 0.51018(13) 0.18294(10) 0.0171(2) Uani 1 1 d . . . . .
C3Q C 0.26239(19) 0.62592(14) 0.12325(11) 0.0215(2) Uani 1 1 d . . . . .
H3Q H 0.2706 0.7188 0.1635 0.026 Uiso 1 1 calc R U . . .
C4Q C 0.2632(2) 0.60351(15) 0.00368(12) 0.0250(3) Uani 1 1 d . . . . .
H4Q H 0.2736 0.6813 -0.0387 0.030 Uiso 1 1 calc R U . . .
C5Q C 0.2487(2) 0.46738(16) -0.05229(12) 0.0259(3) Uani 1 1 d . . . . .
H5Q H 0.2443 0.4487 -0.1346 0.031 Uiso 1 1 calc R U . . .
C6Q C 0.24054(19) 0.35748(15) 0.01323(11) 0.0226(2) Uani 1 1 d . . . . .
H6Q H 0.2324 0.2639 -0.0255 0.027 Uiso 1 1 calc R U . . .
O2 O -0.3759(4) 0.9423(3) 0.0567(2) 0.0361(5) Uani 0.5 1 d D . P . .
H2A H -0.356(4) 0.965(4) -0.0079(14) 0.058(14) Uiso 0.5 1 d D . P . .
H2B H -0.479(3) 0.961(4) 0.070(2) 0.090(19) Uiso 0.5 1 d D . P . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Mn Mn 0.3368 0.7283 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
O1B Mn1 N1P 83.49(13) . .
O1B Mn1 N2R 78.23(11) . .
N1P Mn1 N2R 71.02(4) . .
O1B Mn1 N1Q 85.58(13) . .
N1P Mn1 N1Q 141.97(4) . .
N2R Mn1 N1Q 71.12(4) . .
N1P Mn1 O1A 91.44(9) . 1_455
N2R Mn1 O1A 89.00(10) . 1_455
N1Q Mn1 O1A 84.50(9) . 1_455
O1B Mn1 Cl1B 92.29(11) . .
N1P Mn1 Cl1B 94.77(8) . .
N2R Mn1 Cl1B 163.56(7) . .
N1Q Mn1 Cl1B 122.02(8) . .
N1P Mn1 Cl1A 110.23(6) . .
N2R Mn1 Cl1A 172.76(3) . .
N1Q Mn1 Cl1A 106.89(6) . .
O1A Mn1 Cl1A 83.85(10) 1_455 .
O1B Mn1 Cl2 168.23(11) . .
N1P Mn1 Cl2 92.62(3) . .
N2R Mn1 Cl2 90.00(3) . .
N1Q Mn1 Cl2 90.79(3) . .
O1A Mn1 Cl2 175.26(9) 1_455 .
Cl1B Mn1 Cl2 99.11(3) . .
Cl1A Mn1 Cl2 97.02(2) . .
Mn1 O1A H1A 118.1(18) 1_655 .
Mn1 O1A H1B 111(2) 1_655 .
H1A O1A H1B 109.27(18) . .
Mn1 O1B H1C 127.0(18) . .
Mn1 O1B H1D 119(2) . .
H1C O1B H1D 109.27(19) . .
C2P N1P C6P 117.69(11) . .
C2P N1P Mn1 117.69(8) . .
C6P N1P Mn1 124.56(9) . .
N1P C2P N1R 117.61(11) . .
N1P C2P C3P 122.93(11) . .
N1R C2P C3P 119.46(11) . .
C4P C3P C2P 118.19(13) . .
C4P C3P H3P 120.9 . .
C2P C3P H3P 120.9 . .
C3P C4P C5P 119.58(13) . .
C3P C4P H4P 120.2 . .
C5P C4P H4P 120.2 . .
C6P C5P C4P 118.37(12) . .
C6P C5P H5P 120.8 . .
C4P C5P H5P 120.8 . .
N1P C6P C5P 123.24(13) . .
N1P C6P H6P 118.4 . .
C5P C6P H6P 118.4 . .
N2R N1R C2P 116.32(10) . .
N2R N1R H1R 121.8 . .
C2P N1R H1R 121.8 . .
C2R N2R N1R 121.55(10) . .
C2R N2R Mn1 121.01(8) . .
N1R N2R Mn1 117.23(7) . .
N2R C2R C2Q 114.01(10) . .
N2R C2R C1M 124.52(11) . .
C2Q C2R C1M 121.44(10) . .
C2R C1M H2M 109.5 . .
C2R C1M H1M 109.5 . .
H2M C1M H1M 109.5 . .
C2R C1M H3M 109.5 . .
H2M C1M H3M 109.5 . .
H1M C1M H3M 109.5 . .
C6Q N1Q C2Q 118.64(10) . .
C6Q N1Q Mn1 124.30(8) . .
C2Q N1Q Mn1 116.88(8) . .
N1Q C2Q C3Q 121.71(11) . .
N1Q C2Q C2R 116.39(10) . .
C3Q C2Q C2R 121.89(11) . .
C2Q C3Q C4Q 118.90(12) . .
C2Q C3Q H3Q 120.5 . .
C4Q C3Q H3Q 120.5 . .
C5Q C4Q C3Q 119.14(12) . .
C5Q C4Q H4Q 120.4 . .
C3Q C4Q H4Q 120.4 . .
C4Q C5Q C6Q 118.99(12) . .
C4Q C5Q H5Q 120.5 . .
C6Q C5Q H5Q 120.5 . .
N1Q C6Q C5Q 122.53(12) . .
N1Q C6Q H6Q 118.7 . .
C5Q C6Q H6Q 118.7 . .
H2A O2 H2B 109.24(19) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Mn1 O1B 2.190(5) .
Mn1 N1P 2.2430(11) .
Mn1 N2R 2.2493(10) .
Mn1 N1Q 2.2500(10) .
Mn1 O1A 2.329(4) 1_455
Mn1 Cl1B 2.3463(9) .
Mn1 Cl1A 2.4619(9) .
Mn1 Cl2 2.5700(3) .
O1A Mn1 2.329(4) 1_655
O1A H1A 0.8400(10) .
O1A H1B 0.8400(10) .
O1B H1C 0.8400(10) .
O1B H1D 0.8400(10) .
N1P C2P 1.3340(16) .
N1P C6P 1.3531(15) .
C2P N1R 1.3872(15) .
C2P C3P 1.3995(17) .
C3P C4P 1.3803(19) .
C3P H3P 0.9500 .
C4P C5P 1.389(2) .
C4P H4P 0.9500 .
C5P C6P 1.375(2) .
C5P H5P 0.9500 .
C6P H6P 0.9500 .
N1R N2R 1.3576(14) .
N1R H1R 0.8800 .
N2R C2R 1.2866(14) .
C2R C2Q 1.4855(16) .
C2R C1M 1.4918(16) .
C1M H2M 0.9800 .
C1M H1M 0.9800 .
C1M H3M 0.9800 .
N1Q C6Q 1.3364(16) .
N1Q C2Q 1.3528(15) .
C2Q C3Q 1.3898(16) .
C3Q C4Q 1.3907(18) .
C3Q H3Q 0.9500 .
C4Q C5Q 1.374(2) .
C4Q H4Q 0.9500 .
C5Q C6Q 1.3884(18) .
C5Q H5Q 0.9500 .
C6Q H6Q 0.9500 .
O2 H2A 0.8402(10) .
O2 H2B 0.8401(10) .
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
C6P N1P C2P N1R -179.27(11)
Mn1 N1P C2P N1R 3.23(14)
C6P N1P C2P C3P 0.28(18)
Mn1 N1P C2P C3P -177.22(9)
N1P C2P C3P C4P -0.80(19)
N1R C2P C3P C4P 178.74(11)
C2P C3P C4P C5P 0.85(19)
C3P C4P C5P C6P -0.4(2)
C2P N1P C6P C5P 0.18(19)
Mn1 N1P C6P C5P 177.49(10)
C4P C5P C6P N1P -0.1(2)
N1P C2P N1R N2R -4.25(16)
C3P C2P N1R N2R 176.19(11)
C2P N1R N2R C2R 177.90(11)
C2P N1R N2R Mn1 3.22(13)
N1R N2R C2R C2Q -179.20(10)
Mn1 N2R C2R C2Q -4.72(14)
N1R N2R C2R C1M -1.01(18)
Mn1 N2R C2R C1M 173.48(9)
C6Q N1Q C2Q C3Q -3.24(17)
Mn1 N1Q C2Q C3Q 172.12(9)
C6Q N1Q C2Q C2R 176.44(10)
Mn1 N1Q C2Q C2R -8.20(13)
N2R C2R C2Q N1Q 8.45(15)
C1M C2R C2Q N1Q -169.81(11)
N2R C2R C2Q C3Q -171.87(11)
C1M C2R C2Q C3Q 9.87(17)
N1Q C2Q C3Q C4Q 1.98(18)
C2R C2Q C3Q C4Q -177.69(11)
C2Q C3Q C4Q C5Q 0.75(19)
C3Q C4Q C5Q C6Q -2.11(19)
C2Q N1Q C6Q C5Q 1.81(18)
Mn1 N1Q C6Q C5Q -173.17(9)
C4Q C5Q C6Q N1Q 0.9(2)
